1-(5-Bromo-2-oxoindolin-3-yl­idene)thio­semicarbazide acetonitrile monosolvate

Fernanda Rosi Soares Pederzolli; Leandro Bresolin; Vanessa Santana Carratu; Aline Locatelli; Adriano Bof de Oliveira

doi:10.1107/S1600536811023786

. 2011 Jun 25;67(Pt 7):o1804. doi: 10.1107/S1600536811023786

1-(5-Bromo-2-oxoindolin-3-ylidene)thiosemicarbazide acetonitrile monosolvate

Fernanda Rosi Soares Pederzolli ^a, Leandro Bresolin ^a,^*, Vanessa Santana Carratu ^a, Aline Locatelli ^b, Adriano Bof de Oliveira ^c

PMCID: PMC3152066 PMID: 21837177

Abstract

In the crystal structure of the title compound, C₉H₇BrN₄OS·C₂H₃N, the molecules are connected via N—H⋯O and N—H⋯S interactions into zigzag chains perpendicular to [001]. The molecules in these chains are additionally linked to acetonitrile solvent molecules through N—H⋯N hydrogen bonding. The molecules are arranged in layers and are stacked in the direction of the c axis indicative of π–π interactions, with distance = 3.381 (7) Å for the C⋯C interaction parallel to [001]. An intramolecular N—H⋯O hydrogen bond is also observed in the main molecule.

Related literature

For the pharmacological properties of isatin-thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain, see: Chiyanzu et al. (2003 ▶). For the synthesis of 5-bromoisatin-3-thiosemicarbazone, see: Campaigne & Archer (1952 ▶).

Experimental

Crystal data

C₉H₇BrN₄OS·C₂H₃N
M _r = 340.21
Monoclinic,
a = 20.017 (4) Å
b = 13.352 (2) Å
c = 13.190 (5) Å
β = 129.258 (2)°
V = 2729.6 (12) Å³
Z = 8
Mo Kα radiation
μ = 3.16 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.16 mm

Data collection

Bruker CCD X8 APEXII diffractometer
10884 measured reflections
3377 independent reflections
2754 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.105
S = 1.09
3377 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023786/nc2233sup1.cif

e-67-o1804-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023786/nc2233Isup2.hkl

e-67-o1804-Isup2.hkl^{(165.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023786/nc2233Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H5⋯O	0.86	2.10	2.769 (3)	134
N4—H6⋯N5	0.86	2.61	3.438 (5)	161
N4—H7⋯Oⁱ	0.86	2.05	2.906 (4)	173
N1—H4⋯Sⁱⁱ	0.86	2.50	3.350 (3)	169

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We gratefully acknowledge Professor Dr Manfredo Hörner (Department of Chemistry, Federal University of Santa Maria, Brazil) for his help and support with the X-ray measurements, and CNPq/FAPERGS for financial support.

supplementary crystallographic information

Comment

Thiosemicarbazone derivatives have a wide range of biological properties. For example, isatin-based synthetic thiosemicarbazones show pharmacological activity against cruzain, falcipain-2 and rhodesain (Chiyanzu et al., 2003). As part of our study of thiosemicarbazone derivatives, we report herein the crystal structure of 5-Bromoisatin-3-thiosemicarbazone acetonitrile solvate.

The crystal structure of the title compound is build of one-dimensional zigzag chain in which the molecules are linked by pairs of N—H···O and N—H···S hydrogen bonding. Each two molecules within these chains are additionally linked by acetonitrile molecules via N—H···N hydrogen bonding and weak C—H···S interactions. The molecules are arranged in layers and are stacked into the direction of the c-axis indicative for π-π-interactions.

Experimental

Starting materials were commercially available and were used without further purification. The synthesis was adapted from a procedure reported previously (Campaigne & Archer, 1952). The hydrochloric acid catalyzed reaction of 5-bromoisatin (8,83 mmol) and thiosemicarbazide (8,83 mmol) in ethanol (50 ml) was refluxed for 6 h. After cooling and filtering, crystals suitable for X-ray diffraction were obtained from an acetonitrile solution.